On February 24, 1972, Rainer, Georg; Riedel, Richard published a patent.Formula: C20H14N2O The title of the patent was 4-(Hydroxymethyl)- and 4-formyl-1-arylpyrazoles. And the patent contained the following:
Thirty title compounds [I, R = CHO or CH2OH; R1 = (substituted) phenyl, 3-pyridyl, 2-furyl, or 2-naphthyl; R2 = H, F, Cl, Br, Me, or MeO], useful as intermediates for pharmaceutical 4-(carboxymethyl)- or 4-(cyanomethyl)-1-arylpyrazoles, were prepared by reacting R1CMe:NNHC6H4R2-p with DMF and POCl3 via I (R = CH:N+Me2ClO4-) (Ia). Saponifying Ia gave I (R = CHO), which on reduction gave I (R = CH2OH). Thus, POCl3 was stirred 1 hr with DMF and treated with p-ClC6H4CMe:NNHPh 6 hr at 70°. The mixture was treated 5 hr with aqueous NaOH at pH 7 to give 99% I (R = CHO, R1 = C6H4Cl-p, R2 = H) (II). II was treated in EtOH and DMF with NaBH4 1 hr at 20-5° to give 93% I (R = CH2OH, R1 = C6H4Cl-p, R2 = H). The experimental process involved the reaction of 3-(Naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde(cas: 36640-53-6).Formula: C20H14N2O
The Article related to pyrazolecarboxaldehyde, hydroxymethylpyrazole, benzenes pyrazolyl, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Formula: C20H14N2O
Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics